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C-H methylation of heteroarenes inspired by radical SAM methyl transferase

Academic Article
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Overview

authors

  • Gui, J.
  • Zhou, Q.
  • Pan, C. M.
  • Yabe, Y.
  • Burns, A. C.
  • Collins, M. R.
  • Ornelas, M. A.
  • Ishihara, Yoshihiro
  • Baran, Phil

publication date

  • April 2014

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A practical C-H functionalization method for the methylation of heteroarenes is presented. Inspiration from Nature's methylating agent, S-adenosylmethionine (SAM), allowed for the design and development of zinc bis(phenylsulfonylmethanesulfinate), or PSMS. The action of PSMS on a heteroarene generates a (phenylsulfonyl)methylated intermediate that can be easily separated from unreacted starting material. This intermediate can then be desulfonylated to the methylated product or elaborated to a deuteriomethylated product, and can divergently access medicinally important motifs. This mild, operationally simple protocol that can be conducted in open air at room temperature is compatible with sensitive functional groups for the late-stage functionalization of pharmacologically relevant substrates.

subject areas

  • Hydrocarbons, Aromatic
  • Methylation
  • Organometallic Compounds
  • S-Adenosylmethionine
  • Sulfinic Acids
  • Transferases
  • Zinc
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Identity

PubMed Central ID

  • PMC3988686

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja5007838

PubMed ID

  • 24611732
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Additional Document Info

start page

  • 4853

end page

  • 4856

volume

  • 136

issue

  • 13

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